| 2025 | $0.00 | Sturbridge to Provincetown Monument (2-Day) |
| 2024 | $22,874.72 | Sturbridge to Provincetown Monument (2-Day) |
| 2023 | $20,425.65 | Sturbridge to Provincetown Monument (2-Day) |
| 2022 | $15,000.68 | Sturbridge to Provincetown Monument (2-Day) |
| 2021 | $10,356.00 | Reimagined |
